Organic light-emitting diode

ABSTRACT

An organic light-emitting diode includes an emission layer, a hole migration transfer region and an electron migration region between the first and the second electrodes. The organic light-emitting diode (OLED) has low driving voltages, higher luminance, higher efficiency, higher color purity and longer lifetime than a conventional OLED.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2013-0014646, filed on Feb. 8, 2013, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND

1. Field

One or more embodiments of the present invention relate to an organiclight-emitting diode.

2. Description of the Related Art

Organic light-emitting diodes (OLEDs), which are self-emitting diodes,have advantages such as wide viewing angles, excellent contrast, quickresponse, high brightness, excellent driving voltage characteristics,and can provide multicolored images.

A typical OLED has a structure including a substrate; and an anode, ahole transport layer (HTL), an second electrode (EML), an electrontransport layer (ETL), and a cathode sequentially stacked on thesubstrate. In this regard, the HTL, the EML, and the ETL are organicthin films formed of organic compounds.

An operating principle of an OLED having the above-described structureis as follows.

When a voltage is applied between the anode and the cathode, holesinjected from the anode move to the EML via the HTL, and electronsinjected from the cathode move to the EML via the ETL. The holes andelectrons recombine in the EML to generate excitons. When the excitonsdrop from an excited state to a ground state, light is emitted.

SUMMARY

Aspects of one or more embodiments of the present invention are directedtoward an organic light-emitting diode having a novel structure.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to one or more embodiments of the present invention, anorganic light-emitting device includes: a substrate; a first electrodeon the substrate; a second electrode opposite to the first electrode; anemission layer between the first electrode and the second electrode; ahole migration transfer region between the first electrode and theemission layer; and an electron migration region between the emissionlayer and the second electrode,

wherein the hole migration region includes a first compound representedby Formula 1, and at least one of the hole migration region and theemission layer includes a second compound represented by Formula 100below:

wherein, in Formula 1,

Ar₁₀₁ and Ar₁₀₂ are, each independently, a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocyclooalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocyclooalkenylene group, a substituted or unsubstituted C₆-Choarylene group, or a substituted or unsubstituted C₂-C₆₀ heteroarylenegroup;

xa and xb are, each independently, an integer from 0 to 5;

R₁₀₁ and R₁₀₉ are, each independently, a substituted or unsubstitutedC₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, or a substituted or unsubstituted C₂-C₆₀ heteroaryl group; and

R₁₀₂ to R₁₀₈, and R₁₁₁ to R₁₁₉ are, each independently, a hydrogen atom,a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂), or —Si(Q₃)(Q₄)(Q₅)(where Q₁ to Q₅ are, each independently, a C₁-C₆₀ alkyl group, a C₁-C₆₀alkoxy group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroaryl group), and

in Formula 100,

i) R₅₆ and R₅₇ are linked to each other to form a substituted orunsubstituted C₃-C₆₀ cyclic moiety, or a substituted or unsubstitutedC₂-C₆₀ heterocyclic moiety, and R₅₁ to R₅₅ and R₅₈ to R₆₀ are, eachindependently, a substituent represented by —(Ar₅₁)_(q)—(Ar₆₁), or

ii) R₅₈ and R₅₉ are linked to each other to form a substituted orunsubstituted C₃-C₆₀ cyclic moiety, or a substituted or unsubstitutedC₂-C₆₀ heterocyclic moiety, and R₅₁ to R₅₇ and R₆₀ are, eachindependently, a substituent represented by —(Ar₅₁)_(q)—(Ar₆₁);

Ar₅₀ and Ar₅₁ are, each independently, a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocyclooalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a C₂-C₁₀ heterocyclooalkenylene group, asubstituted or unsubstituted C₆-C₆₀ arylene group, or a substituted orunsubstituted C₂-C₆₀ heteroarylene group;

Ar₆₀ and Ar₆₁ are, each independently, selected from among a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, —N(Q₂₁)(Q₂₂), and —Si(Q₂₃)(Q₂₄)(Q₂₅) (where Q₂₁ andQ₂₂ are, each independently, selected from among a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, and a substituted or unsubstitutedC₂-C₆₀ heteroaryl group; and Q₂₃ to Q₂₅ are, each independently,selected from among a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, and a substituted or unsubstitutedC₂-C₆₀ heteroaryl group); and

p and q are, each independently, an integer from 0 to 5.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawings of which:

FIG. 1 is a schematic view of a structure of an organic light-emittingdiode according to an embodiment of the present invention;

FIG. 2 is a schematic view of a structure of an organic light-emittingdiode according to another embodiment of the present invention; and

FIG. 3 is a schematic view of a structure of an organic light-emittingdiode according to another embodiment of the present invention.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of the present description. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. Expressions such as “at least oneof,” when preceding a list of elements, modify the entire list ofelements and do not modify the individual elements of the list.

Further, the use of “may” when describing embodiments of the presentinvention refers to “one or more embodiments of the present invention.”

Referring to FIG. 1, an organic light emitting diode 10 according to anembodiment of the present invention has a structure including asubstrate 11, a first electrode 12, a hole migration region 13, anemission layer (EML) 15, an electron migration region 17, and a secondelectrode 19 that are sequentially stacked on one another.

The substrate 11 may be any substrate that is used in existing organiclight-emitting diodes. In some embodiments, the substrate 11 may be aglass substrate or a transparent plastic substrate with strongmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance.

The first electrode 12 may be formed by depositing or sputtering a firstelectrode-forming material on the substrate 11. When the first electrode12 is an anode, a material having a high work function may be used asthe first electrode-forming material to facilitate hole injection. Thefirst electrode 12 may be a reflective electrode or a transmissionelectrode. Transparent and conductive materials (such as ITO, IZO, SnO₂,or ZnO) may be used to form the first electrode 12. The first electrode12 may be formed as a reflective electrode using magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), magnesium-silver (Mg—Ag), or the like.

The first electrode 12 may have a single-layer structure or amulti-layer structure including at least two layers. For example, thefirst electrode 12 may have a three-layered structure of ITO/Ag/ITO, butis not limited thereto.

The first electrode 12 may be a hole-injecting electrode (anode).

In one embodiment, the second electrode 19 is disposed opposite to thefirst electrode 12. The second electrode 19 may be a cathode, which isan electron injecting electrode. A metal for forming the secondelectrode 19 may be a metal, an alloy, an electrically conductivecompound, which have a low-work function, or a mixture thereof. In thisregard, the second electrode 19 may be formed of lithium (Li), magnesium(Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), magnesium(Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like, and may beformed as a thin film type transmission electrode. In some embodiments,to manufacture a top-emission light-emitting diode, the transmissionelectrode may be formed of indium tin oxide (ITO) or indium zinc oxide(IZO).

In one embodiment, the EML 15 is disposed between the first electrode 12and the second electrode, the hole migration region 13 is disposedbetween the first electrode 12 and the EML 15, and the electronmigration region 17 is disposed between the EML 15 and the secondelectrode 19.

In the organic light-emitting diode 10 according to one embodiment,holes are injected through the first electrode 12 to migrate to the EML15 through the hole migration region 13, while electrons are injectedthrough second electrode 19 to migrate to the EML 15 through theelectron migration region 17. The holes and electrons recombine in theEML 15 to generate excitons. When the excitons drop from an excitedstate to a ground state, light is emitted.

The hole migration region 13 may include at least one layer. That is,the hole migration region 13 may have a single-layered structure or alaminated structure of at least two layers. The electron migrationregion 17 may include at least one layer. That is, the electronmigration region 17 may have a single-layered structure or a laminatedstructure of at least two layers.

In one embodiment, the hole migration region 13 includes a firstcompound represented by Formula 1 below, and at least one of the holemigration region 13 and the EML 15 includes a second compoundrepresented by Formula 100 below.

In Formula 1, Ar₁₀₁ and Ar₁₀₂ may be, each independently, a substitutedor unsubstituted C₃-C₁₀ cycloalkylene group, a substituted orunsubstituted C₂-C₁₀ heterocyclooalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₂-C₁₀ heterocyclooalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, or a substituted or unsubstitutedC₂-C₆₀ heteroarylene group.

For example, in Formula 1, Ar₁₀₁ and Ar₁₀₂ may be, each independently,selected from a substituted or unsubstituted phenylene group, asubstituted or unsubstituted pentalenylene group, a substituted orunsubstituted indenylene group, a substituted or unsubstitutednaphthylene group, a substituted or unsubstituted azulenylene group, asubstituted or unsubstituted heptalenylene group, a substituted orunsubstituted indacenylene group, a substituted or unsubstitutedacenaphthylene group, a substituted or unsubstituted fluorenylene group,a substituted or unsubstituted spiro-fluorenylene group, a substitutedor unsubstituted phenalenylene group, a substituted or unsubstitutedphenanthrenylene group, a substituted or unsubstituted anthrylene group,a substituted or unsubstituted fluoranthenylene group, a substituted orunsubstituted triphenylenylene group, a substituted or unsubstitutedpyrenylene group, a substituted or unsubstituted chrysenylene group, asubstituted or unsubstituted naphthacenylene group, a substituted orunsubstituted picenylene group, a substituted or unsubstitutedperylenylene group, a substituted or unsubstituted pentaphenylene group,a substituted or unsubstituted hexacenylene group, a substituted orunsubstituted pyrrolylene group, a substituted or unsubstitutedimidazolylene group, a substituted or unsubstituted pyrazolylene group,a substituted or unsubstituted pyridinylene group, a substituted orunsubstituted pyrazinylene group, a substituted or unsubstitutedpyrimidinylene group, a substituted or unsubstituted pyridazinylenegroup, a substituted or unsubstituted isoindolylene group, a substitutedor unsubstituted indolylene group, a substituted or unsubstitutedindazolylene group, a substituted or unsubstituted purinylene group, asubstituted or unsubstituted quinolinylene group, a substituted orunsubstituted benzo quinolinylene group, a substituted or unsubstitutedphthalazinylene group, a substituted or unsubstituted naphthyridinylenegroup, a substituted or unsubstituted quinoxalinylene group, asubstituted or unsubstituted quinazolinylene group, a substituted orunsubstituted cinnolinylene group, a substituted or unsubstitutedcarbazolylene group, a substituted or unsubstituted phenanthridinylenegroup, a substituted or unsubstituted acridinylene group, a substitutedor unsubstituted phenanthrolinylene group, a substituted orunsubstituted phenazinylene group, a substituted or unsubstitutedbenzooxazolylene group, a substituted or unsubstitutedbenzoimidazolylene group, a substituted or unsubstituted furanylenegroup, a substituted or unsubstituted benzofuranylene group, asubstituted or unsubstituted thiophenylene group, a substituted orunsubstituted benzothiophenylene group, a substituted or unsubstitutedthiazolylene group, a substituted or unsubstituted isothiazolylenegroup, a substituted or unsubstituted benzothiazolylene group, asubstituted or unsubstituted isoxazolylene group, a substituted orunsubstituted oxazolylene group, a substituted or unsubstitutedtriazolylene group, a substituted or unsubstituted tetrazolylene group,a substituted or unsubstituted oxadiazolylene group, a substituted orunsubstituted triazinylene group, a substituted or unsubstitutedbenzooxazolylene group, a substituted or unsubstituted dibenzofuranylenegroup, a substituted or unsubstituted dibenzothiophenylene group, and asubstituted or unsubstituted benzocarbazolyl group.

In some embodiments, Ar₁₀₁ and Ar₁₀₂ in Formula 1 may be, eachindependently, represented by one of Formulae 3-1 to 3-24:

In Formulae 3-1 to 3-24, Y₁ may be O, S, C(R₂₁)(R₂₂), or N(R₂₃).

In Formulae 3-1 to 3-24, Z₁, Z₂, and R₂₁ to R₂₃ may be, eachindependently, selected from among,

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroaryl group;

a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroaryl group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

—N(Q₁₁)(Q₁₂) and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅ are, eachindependently, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₆-C₂₀arylgroup, or a C₂-C₂₀heteroaryl group).

For example, Z₁, Z₂, and R₂₁ to R₂₃ may be, each independently, selectedfrom among,

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

—N(Q₁₁)(Q₁₂) and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅ are, eachindependently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, aphenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group), but are not limited thereto.

In Formulae 3-1 to 3-24 above, d1 may be an integer from 1 to 4; d2 maybe an integer from 1 to 3; d3 may be an integer from 1 to 6; d4 may bean integer from 1 to 8; and d5 may be an integer of 1 or 2.

In some embodiments, Ar₁₀₁, Ar₁₀₂, Ar₁, and Ar₂ in Formula 1 may be,each independently, represented by one of Formulae 4-1 to 4-7 below, butare not limited thereto:

In Formula 1 above, xa indicates number of Ar₁₀₁s, and xb indicatesnumber of Ar₁₀₂s, wherein xa and xb may be, each independently, aninteger from 0 to 5. When xa and/or xb is 0, “carbazole” and/or“fluorene” in Formula 1 may be linked directly to “N”. When xa is 2 orgreater, the at least two of Ar₁₀₁s may be identical to or differentfrom each other. When xb is 2 or greater, the at least two of Ar₁₀₂s maybe identical to or different from each other.

In some embodiments, in Formula 1, i) xa=0 and xb=0; ii) xa=1 and xb=0;iii) xa=2 and xb=0; iv) xa=0 and xb=1; v) xa=0 and xb=2; or vi) xa=1 andxb=1, but not limited thereto.

In Formula 1, R₁₀₁ and R₁₀₉ may be, each independently, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, or a substituted or unsubstituted C₂-C₆₀ heteroaryl group.

For example, in Formula 1, R₁₀₁ and R₁₀₉ may be, each independently,selected from a substituted or unsubstituted phenyl group, a substitutedor unsubstituted pentalenyl group, a substituted or unsubstitutedindenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted azulenyl group, a substituted orunsubstituted heptalenyl group, a substituted or unsubstituted indacenylgroup, a substituted or unsubstituted acenaphthyl group, a substitutedor unsubstituted fluorenyl group, a substituted or unsubstitutedspiro-fluorenyl group, a substituted or unsubstituted phenalenyl group,a substituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthryl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenylenyl group,a substituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstitutednaphthacenyl group, a substituted or unsubstituted picenyl group, asubstituted or unsubstituted perylenyl group, a substituted orunsubstituted pentaphenyl group, a substituted or unsubstitutedhexacenyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted imidazolyl group, a substituted orunsubstituted pyrazolyl group, a substituted or unsubstituted pyridinylgroup, a substituted or unsubstituted pyrazinyl group, a substituted orunsubstituted pyrimidinyl group, a substituted or unsubstitutedpyridazinyl group, a substituted or unsubstituted isoindolyl group, asubstituted or unsubstituted indolyl group, a substituted orunsubstituted indazolyl group, a substituted or unsubstituted purinylgroup, a substituted or unsubstituted quinolinyl group, a substituted orunsubstituted benzoquinolinyl group, a substituted or unsubstitutedphthalazinyl group, a substituted or unsubstituted naphthyridinyl group,a substituted or unsubstituted quinoxalinyl group, a substituted orunsubstituted quinazolinyl group, a substituted or unsubstitutedcinnolinyl group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted phenanthridinyl group, a substituted orunsubstituted acridinyl group, a substituted or unsubstitutedphenanthrolinyl group, a substituted or unsubstituted phenazinyl group,a substituted or unsubstituted benzooxazolyl group, a substituted orunsubstituted benzoimidazolyl group, a substituted or unsubstitutedfuranyl group, a substituted or unsubstituted benzofuranyl group, asubstituted or unsubstituted thiophenyl group, a substituted orunsubstituted benzothiophenyl group, a substituted or unsubstitutedthiazolyl group, a substituted or unsubstituted isothiazolyl group, asubstituted or unsubstituted benzothiazolyl group, a substituted orunsubstituted isoxazolyl group, a substituted or unsubstituted oxazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted tetrazolyl group, a substituted or unsubstitutedoxadiazolyl group, a substituted or unsubstituted triazinyl group, asubstituted or unsubstituted benzooxazolyl group, a substituted orunsubstituted dibenzopuranyl group, a substituted or unsubstituteddibenzothiophenyl group, and a substituted or unsubstitutedbenzocarbazolyl group.

In some other embodiments, R₁₀₁ and R₁₀₉ may be, each independently,represented by one of Formulae 5-1 to 5-22 below:

In Formulae 5-1 to 5-22, Y₂ may be O, S, C(R₂₅)(R₂₆), or N(R₂₇).

In Formulae 5-1 to 5-22, Z₁₁ to Z₁₄, and R₂₅ to R₂₇ may be, eachindependently, selected from among,

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a C₆-C₂₀ aryl group, and a C₂-C₂₀ heteroaryl group;

a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroaryl group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group C₂-C₆₀ alkynyl group, C₁-C₆₀ alkoxy group,a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, aphenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group; and

—N(Q₁₁)(Q₁₂) and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅ are, eachindependently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀aryl group, or a C₂-C₂₀ heteroaryl group).

For example, Z₁₁ to Z₁₄, and R₂₅ to R₂₇ in Formulae 5-1 to 5-22 may be,each independently, selected from among,

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

—N(Q₁₁)(Q₁₂) and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅ are, eachindependently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, aphenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group), but are not limited thereto.

In Formulae 5-1 to 5-22, e1 may be an integer from 1 to 5; e2 may be aninteger from 1 to 7; e3 may be an integer from 1 to 3; e4 may be aninteger from 1 to 4; and e5 may be an integer of 1 or 2.

For example, R₁₀₁ in Formula 1 may be a group represented by one ofFormulae 6-1 to 6-8 below, and R₁₀₉ in Formula 1 may be a grouprepresented by one of Formulae 6-1 to 6-11 below:

In Formulae 6-1 to 6-11, Z_(11a) to Z_(11c) may be defined the same asZ₁₁ described above, and R₂₅, R₂₆, Q₁₁, and Q₁₂ may be defined the sameas described above.

For example, in Formulae 6-1 to 6-11, Z_(11a) to Z_(11c), R₂₅, and R₂₆may be, each independently, selected from among,

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group; and

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

Q₁₁ and Q₁₂ may be, each independently, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, or an isoquinolinyl group.

For example, R₁₁₁ and R₁₁₂ in Formula 1 may be, each independently,selected from among

a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one of a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, and a phosphoricacid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group; and

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group.

In Formula 100, R₅₆ and R₅₇ may be linked to each other to form asubstituted or unsubstituted C₃-C₆₀ cyclic moiety, or a substituted orunsubstituted C₂-C₆₀ heterocyclic moiety, and R₅₁ to R₅₅ and R₅₈ to R₆₀may be, each independently, a substituent represented by—(Ar₅₁)_(q)—(Ar₆₁). In some embodiments, in Formula 100, R₅₈ and R₅₉ maybe linked to each other to form a substituted or unsubstituted C₃-C₆₀cyclic moiety, or a substituted or unsubstituted C₂-C₆₀ heterocyclicmoiety, and R₅₁ to R₅₇ and R₆₀ may be, each independently, a substituentrepresented by —(Ar₅₁)_(q)—(Ar₆₁).

The second compound may be a compound represented by Formula 100A or100B below:

In Formulae 100A and 100B, Ar₅₀, Ar₆₀, p, and R₅₁ to R₆₀ may be the sameas those described above.

In Formulae 100A and 100B, P ring and Q ring may be, each independently,selected from among,

i) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene; and

ii) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene, substituted with one selected from among

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₆₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, and

—N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ may be, each independently, a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group).

In some embodiments, R₅₁ to R₅₄ in Formulae 100A and 100B may all behydrogen atoms.

In some other embodiments, the second compound may be a compoundrepresented by one of Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9,but is not limited thereto:

In Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9,

R₅₁ to R₆₀, Ar₅₀, Ar₆₀, and p may be the same as those described above;

X₁₂ may be O, S, C(R₇₁)(R₇₂), or N(R₇₃);

R₆₁, R₆₂, and R₇₁ to R₇₃ may be, each independently, selected from among

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof,

a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₅₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group,

a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group, substituted with at least one of a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup, and

—N(Q₁₁)(Q₁₂), and —Si(Q₁₁)(Q₁₂)(Q₁₃) (where Q₁₁ and Q₁₂ may be, eachindependently, a C₆-C₆₀ aryl group or a C₂-C₆₀ heteroaryl group, and Q₁₃to Q₁₅ are, each independently, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxygroup, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroaryl group);

r1 may be an integer from 1 to 4; r2 may be 1 or 2; and r3 may be aninteger from 1 to 6.

For example, in Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9, R₆₁,R₆₂, and R₇₁ to R₇₃ may be, each independently, selected from among

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₆₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, and

—N(Q₁₁)(Q₁₂), and —Si(Q₁₁)(Q₁₂)(Q₁₃) (where Q₁₁ and Q₁₂ may be, eachindependently, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, or an isoquinolinyl group; and Q₁₃ to Q₁₅ maybe, each independently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group), but are not limited thereto.

In Formula 100, Ar₅₀ and Ar₅₁ may be, each independently, selected froma substituted or unsubstituted phenylene group, a substituted orunsubstituted pentalenylene group, a substituted or unsubstitutedindenylene group, a substituted or unsubstituted naphthylene group, asubstituted or unsubstituted azulenylene group, a substituted orunsubstituted heptalenylene group, a substituted or unsubstitutedindacenylene group, a substituted or unsubstituted acenaphthylene group,a substituted or unsubstituted fluorenylene group, a substituted orunsubstituted spiro-fluorenylene group, a substituted or unsubstitutedphenalenylene group, a substituted or unsubstituted phenanthrenylenegroup, a substituted or unsubstituted anthrylene group, a substituted orunsubstituted fluoranthenylene group, a substituted or unsubstitutedtriphenylenylene group, a substituted or unsubstituted pyrenylene group,a substituted or unsubstituted chrysenylene group, a substituted orunsubstituted naphthacenylene group, a substituted or unsubstitutedpicenylene group, a substituted or unsubstituted perylenylene group, asubstituted or unsubstituted pentaphenylene group, a substituted orunsubstituted hexacenylene group, a substituted or unsubstitutedpyrrolylene group, a substituted or unsubstituted imidazolylene group, asubstituted or unsubstituted pyrazolylene group, a substituted orunsubstituted pyridinylene group, a substituted or unsubstitutedpyrazinylene group, a substituted or unsubstituted pyrimidinylene group,a substituted or unsubstituted pyridazinylene group, a substituted orunsubstituted isoindolylene group, a substituted or unsubstitutedindolylene group, a substituted or unsubstituted indazolylene group, asubstituted or unsubstituted purinylene group, a substituted orunsubstituted quinolinylene group, a substituted or unsubstitutedbenzoquinolinylene group, a substituted or unsubstituted phthalazinylenegroup, a substituted or unsubstituted naphthyridinylene group, asubstituted or unsubstituted quinoxalinylene group, a substituted orunsubstituted quinazolinylene group, a substituted or unsubstitutedcinnolinylene group, a substituted or unsubstituted carbazolylene group,a substituted or unsubstituted phenanthridinylene group, a substitutedor unsubstituted acridinylene group, a substituted or unsubstitutedphenanthrolinylene group, a substituted or unsubstituted phenazinylenegroup, a substituted or unsubstituted benzooxazolylene group, asubstituted or unsubstituted benzoimidazolylene group, a substituted orunsubstituted furanylene group, a substituted or unsubstitutedbenzofuranylene group, a substituted or unsubstituted thiophenylenegroup, a substituted or unsubstituted benzothiophenylene group, asubstituted or unsubstituted thiazolylene group, a substituted orunsubstituted isothiazolylene group, a substituted or unsubstitutedbenzothiazolylene group, a substituted or unsubstituted isoxazolylenegroup, a substituted or unsubstituted oxazolylene group, a substitutedor unsubstituted triazolylene group, a substituted or unsubstitutedtetrazolylene group, a substituted or unsubstituted oxadiazolylenegroup, a substituted or unsubstituted triazinylene group, a substitutedor unsubstituted benzooxazolylene group, a substituted or unsubstituteddibenzopuranylene group, a substituted or unsubstituteddibenzothiophenylene group, and a substituted or unsubstitutedbenzocarbazolylene group, but are not limited thereto.

In some embodiments, in Formula 100, Ar₅₀ and Ar₅₁ may be, eachindependently, selected from among

i) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzofuranylene group, and adibenzothiophenylene group, and

ii) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzofuranylene group, and adibenzothiophenylene group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylicgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group.

In some other embodiments, in Formula 100, Ar₅₀ and Ar₅₁ may be, eachindependently, selected from among groups represented by Formulae 102-1to 102-5:

In Formulae 102-1 to 102-5, Z₂₁ and Z₂₂ may be, each independently,selected from among a hydrogen atom, a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenylgroup, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group;

f₁ may be an integer from 1 to 3;

f₂ may be an integer from 1 to 4;

* indicates a binding site of a core in Formula 1, or a binding site ofother Ar₅₀ or Ar₆₁ spaced from the core of Formula 1;

*′ indicates a binding site of Ar₅₀ or Ar₅₁ spaced from the core ofFormula 1, or a binding site of Ar₆₀ or Ar₆₁.

In Formula 100, Ar₆₀ and Ar₆₁ may be, each independently, selected fromamong a substituted or unsubstituted phenyl group, a substituted orunsubstituted pentalenyl group, a substituted or unsubstituted indenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted azulenyl group, a substituted or unsubstituted heptalenylgroup, a substituted or unsubstituted indacenyl group, a substituted orunsubstituted acenaphtyl group, a substituted or unsubstituted fluorenylgroup, a substituted or unsubstituted spiro-fluorenyl group, asubstituted or unsubstituted phenalenyl group, a substituted orunsubstituted phenanthrenyl group, a substituted or unsubstitutedanthryl group, a substituted or unsubstituted fluoranthenyl group, asubstituted or unsubstituted triphenylenyl group, a substituted orunsubstituted pyrenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted naphthacenyl group, a substitutedor unsubstituted picenyl group, a substituted or unsubstituted perylenylgroup, a substituted or unsubstituted pentaphenyl group, a substitutedor unsubstituted hexacenyl group, a substituted or unsubstitutedpyrrolyl group, a substituted or unsubstituted imidazolyl group, asubstituted or unsubstituted pyrazolyl group, a substituted orunsubstituted pyridinyl group, a substituted or unsubstituted pyrazinylgroup, a substituted or unsubstituted pyrimidinyl group, a substitutedor unsubstituted pyridazinyl group, a substituted or unsubstitutedisoindolyl group, a substituted or unsubstituted indolyl group, asubstituted or unsubstituted indazolyl group, a substituted orunsubstituted purinyl group, a substituted or unsubstituted quinolinylgroup, a substituted or unsubstituted benzoquinolinyl group, asubstituted or unsubstituted phthalazinyl group, a substituted orunsubstituted naphthyridinyl group, a substituted or unsubstitutedquinoxalinyl group, a substituted or unsubstituted quinazolinyl group, asubstituted or unsubstituted cinnolinyl group, a substituted orunsubstituted carbazolyl group, a substituted or unsubstitutedphenanthridinyl group, a substituted or unsubstituted acridinyl group, asubstituted or unsubstituted phenanthrolinyl group, a substituted orunsubstituted phenazinyl group, a substituted or unsubstitutedbenzooxazolyl group, a substituted or unsubstituted benzoimidazolylgroup, a substituted or unsubstituted furanyl group, a substituted orunsubstituted benzofuranyl group, a substituted or unsubstitutedthiophenyl group, a substituted or unsubstituted benzothiophenyl group,a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted isothiazolyl group, a substituted or unsubstitutedbenzothiazolyl group, a substituted or unsubstituted isoxazolyl group, asubstituted or unsubstituted oxazolyl group, a substituted orunsubstituted triazolyl group, a substituted or unsubstituted tetrazolylgroup, a substituted or unsubstituted oxadiazolyl group, a substitutedor unsubstituted triazinyl group, a substituted or unsubstitutedbenzooxazolyl group, a substituted or unsubstituted dibenzopuranylgroup, a substituted or unsubstituted dibenzothiophenyl group, asubstituted or unsubstituted benzocarbazolylene group, and —N(Q₂₁)(Q₂₂)(where Q₂₁ and Q₂₂ may be, each independently, a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenylgroup, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, or anisoquinolinyl group).

In some other embodiments, Ar₆₀ and Ar₆₁ in Formula 100 may be, eachindependently, selected from among groups represented by Formulae 103-1to 103-16:

In Formulae 103-1 to 103-16,

Y₂₁ may be O, S, C(Z₄₁)(Z₄₂), or N(Z₄₃);

Z₃₁, Z₃₂, and Z₄₁ to Z₄₃ may be, each independently, selected from amonga hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup;

Q₂₁ and Q₂₂ may be, each independently, selected from among a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group;

g1 may be an integer from 1 to 5; g2 may be an integer from 1 to 7; g3may be an integer from 1 to 3; g4 may be an integer from 1 to 4; and g5may be 1 or 2. However, embodiments of the present invention are notlimited thereto.

In Formula 100, “p” in —(Ar₅₀)_(p)-(Ar₆₀) indicates the number of Ar₅₀s,and may be an integer from 0 to 5. When p is 0, Ar₆₀ may be directlylinked to nitrogen in Formula 100. When p is 2 or greater, the two ormore Ar₅₀s may be identical to or differ from each other. In Formula100, “q” in —(Ar₅₁)_(q)—(Ar₆₁) indicates the number of Ar₅₁s, and may bean integer from 0 to 5. When q is 0, Ar₆₁ may be directly linked to thecore of Formula 100. When q is 2 or greater, the two or more Ar₅₁s maybe identical to or differ from each other.

In some embodiments, the first compound may be a compound represented byFormula 1A, 1B, or 1C below:

The substitutents in Formulae 1A, 1B, and 1C may be the same as thosedescribed above.

For example, in Formulae 1A, 1B, and 1C,

Ar₁₀₁ and Ar₁₀₂ may be, each independently, a group represented by oneof Formulae 3-1 to 3-24;

xa and xb may be, each independently, 1 or 2;

R₁₀₁ and R₁₀₉ may be, each independently, a group represented by one ofFormulae 5-1 to 5-22;

R₁₁₁ and R₁₁₂ may be, each independently, one selected from among

a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one of a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, and a phosphoricacid group or a salt thereof,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, and

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

R₁₀₂ to R₁₀₈ and R₁₁₃ to R₁₁₉ may be, each independently, selected fromamong

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, and

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, but are notlimited thereto.

For example, in Formulae 1A, 1B, and 1C,

Ar₁₀₁ and Ar₁₀₂ may be, each independently, a group represented by oneof Formulae 4-1 to 4-7;

xa and xb may be, each independently, 1 or 2;

R₁₀₁ may be a group represented by one of Formulae 6-1 to 6-8;

R₁₀₉ may be a group represented by one of Formulae 6-1 to 6-11;

R₁₁₁ and R₁₁₂ may be, each independently, one selected from among

a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one of a deuterium atom,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, and a phosphoricacid group or a salt thereof;

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group; and

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfuorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and

R₁₀₂ to R₁₀₈ and R₁₁₃ to R₁₁₉ may be hydrogen atoms.

In some other embodiments, the second compound may be represented byFormula 100A-HLT or 100B-HLT.

The substituents in Formulae 100A-HLT and 100B-HLT may be the same asthose described above.

For example, in Formulae 100A-HLT and 100B-HLT,

P ring and Q ring may be, each independently, selected from among

i) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene; and

ii) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene, substituted with at least one selected from among

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₆₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, and

—N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ are, each independently, a phenyl group,a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group);

Ar₅₀ and Ar₅₁ may be, each independently, selected from among

i) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzopuranylene group, and adibenzothiophenylene group, and

ii) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzopuranylene group, and adibenzothiophenylene group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group;

p and q may be, each independently, 0, 1, or 2; and

Ar₆₁, Q₂₁, and Q₂₂ may be, each independently, selected from among aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group.

In some embodiments, the second compound may be a compound representedby Formula 100A-H1 or 100B-H1 below:

The substituents in Formulae 100A-H1 and 100B-H1 may be the same asthose described above.

For example, in Formulae 100A-H1 and 100B-H1,

P ring and Q ring may be, each independently, selected from among

i) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene, and

ii) benzene, naphthalene, fluorene, carbazole, dibenzofuran, anddibenzothiophene, substituted with at least one selected from among

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group,

a C₁-C₂₀ alkyl group and a C₁-C₆₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group,

a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, acarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, andan isoquinolinyl group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, and

—N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ may be, each independently, a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group);

Ar₅₀ and Ar₅₁ may be, each independently, selected from among

i) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzopuranylene group, and adibenzothiophenylene group, and

ii) a phenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzopuranylene group, and adibenzothiophenylene group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group;

p and q may be, each independently, 0, 1, or 2;

Z₂₁ and Z₂₂ may be, each independently, selected from among a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup;

f1 and f2 may be, each independently, 0, 1, or 2; and

Ar₆₀ and Ar₆₁ may be, each independently, selected from among groupsrepresented by Formulae 103-1 to 103-16.

In some other embodiments, the first compound of Formula 1 may be one ofCompounds 1-1 to 1-19 below, but is not limited thereto:

In some other embodiments, the second compound of Formula 100 may be oneof Compounds 2-1 to 2-30 below, but is not limited thereto:

At least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₂-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₂-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₂-C₆₀heteroarylene group, the substituted C₃-C₁₀ cycloalkyl group thesubstituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₂-C₆₀ heteroaryl group,the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenylgroup, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₆-C₆₀ aryloxy group, and the substitutedC₆-C₆₀ arylthio group may be selected from among,

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine, a hydrazone,a carboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof;

a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and aC₂-C₆₀ heteroaryl group;

a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group, substituted with at least one of a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,C₂-C₆₀ alkynyl group, C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; and

—Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₃ to Q₁₅ may be, each independently, aC₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, or aC₂-C₆₀ heteroaryl group), but not limited thereto.

The first compound of Formula 1 above has good charge (hole)transporting ability. The second compound of Formula 100 above has goodcharge (hole) transporting ability, good light-emitting ability, and hasa high band gap energy between the highest occupied molecular orbital(HOMO) and lowest unoccupied molecular orbital (LUMO), and thus allowseasy energy level adjustment. When including the first compound in thehole migration region 13 and the second compound in at least one of thehole migration region 13 and the EML 15, the organic light-emittingdiode 10 may have a low driving voltage, a high luminance, a highefficiency, and a long lifetime.

In some embodiments, the first compound of Formula 1 and the secondcompound of Formula 100 may be both in the hole migration region 13.

In some other embodiments, the first compound of Formula 1 above may bein the hole migration region 13, and the second compound of Formula 100above may be in the EML 15.

In some other embodiments, the first compound of Formula 1 above and thesecond compound of Formula 100 above may be both in the hole migrationregion 13, and the second compound of Formula 100 above may be in theEML 15. In this regard, the second compound in the hole migration region13 and the second compound in the EML 15 may be the same or differentfrom each other.

FIG. 2 is a schematic view of a structure of an organic light-emittingdiode 20 according to another embodiment of the present invention.Referring to FIG. 2, the organic light emitting diode 20 has a structureincluding a substrate 21, a first electrode 22, a hole migration region23, an emission layer (EML) 25, an electron migration region 27, and asecond electrode 29 that are sequentially stacked on one another. Thehole migration region 23 includes a hole injection layer (HIL) 23A, afirst hole transport layer (HTL) 23B-1, and a second HTL 23B-2 that aresequentially stacked on the first electrode 22. The electron migrationregion 27 includes an electron transport layer (ETL) 27A and an electroninjection layer (EIL) 27B that are sequentially stacked on the EML 25.

The above-detailed descriptions of the substrate 11, the first electrode12, and the second electrode 19 may be referred to as detaileddescriptions of the substrate 21, the first electrode 22, and the secondelectrode 29 of FIG. 2.

The HIL 23A may be formed on the first electrode 22 by any of a varietyof methods, including vacuum deposition, spin coating, casting, andLangmuir-Blodgett (LB) deposition.

When the HIL 23A is formed using vacuum deposition, vacuum depositionconditions may vary according to the compound that is used to form theHIL 23A, and the desired structure and thermal properties of the HIL 23Ato be formed. For example, vacuum deposition may be performed at atemperature of about 100° C. to about 500° C., a pressure of about 10⁻⁸torr to about 10⁻³ torr, and a deposition rate of about 0.01 to about100 Å/sec. However, the deposition conditions are not limited thereto.

When the HIL 23A is formed using spin coating, the coating conditionsmay vary according to the compound that is used to form the HIL 23A, andthe desired structure and thermal properties of the HIL 23A to beformed. For example, the coating rate may be in the range of about 2000rpm to about 5000 rpm, and a temperature at which heat treatment isperformed to remove a solvent after coating may be in the range of about80° C. to about 200° C. However, the coating conditions are not limitedthereto.

Non-limiting examples of materials for the HIL 23A areN,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound (such as copperphthalocyanine),4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA, 2-TNATA,polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA), andpolyaniline)/poly(4-styrenesulfonate (PANI/PSS):

The thickness of the HIL 23A may be from about 100 Å to about 10000 Å,and in some embodiments, may be from about 100 Å to about 1000 Å. Whenthe thickness of the HIL 23A is within these ranges, the HIL 23A mayhave good hole injecting ability without a substantial increase indriving voltage.

Then, a first HTL 23B-1 may be formed on the HIL 23A by using any of avariety of methods, for example, vacuum deposition, spin coating,casting, Langmuir-Blodgett (LB) deposition, or the like. When the firstHTL 23B-1 is formed using vacuum deposition or spin coating, theconditions for deposition and coating may be similar to those for theformation of the HIL 23A, although the conditions for the deposition andcoating may vary depending on the material that is used to form thefirst HTL 23B-1.

The first HTL 23B-1 may be formed using the first compound representedby Formula 1 above. The above-detailed description of Formula 1A abovemay be referred to here. For example, the first HTL 23B-1 may include afirst compound represented by Formula 1A, 1B, or 1C above, wherein, inFormula 1A, 1B, and 1C, Ar₁₀₁ and Ar₁₀₂ may be, each independently, agroup represented by one of Formulae 4-1 to 4-7; xa and xb may be, eachindependently, 1 or 2; R₁₀₁ may be a group represented by one ofFormulae 6-1 to 6-8; R₁₀₉ may be a group represented by one of Formulae6-1 to 6-11; R₁₁₁ and R₁₁₂ may be, each independently, one of a C₁-C₂₀alkyl group; a C₁-C₂₀ alkyl group substituted with at least one of adeuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine, a hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, and a phosphoric acid group or a salt thereof; a phenyl group,a naphthyl group, an anthryl group, a fluorenyl group, a carbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group; and a phenyl group, a naphthyl group, an anthrylgroup, a fluorenyl group, a carbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; and R₁₀₂ to R₁₀₈ and R₁₁₃ to R₁₁₉ may be hydrogen atoms.

In some other embodiments, a material for the first HTL 23B-1 may be oneof Compounds 1-1 to 1-19 above.

Then, a second HTL 23B-2 may be formed on the first HIL 23B-1 by usingany of a variety of methods, for example, vacuum deposition, spincoating, casting, Langmuir-Blodgett (LB) deposition, or the like. Whenthe second HTL 23B-2 is formed using vacuum deposition or spin coating,the conditions for deposition and coating may be similar to those forthe formation of the HIL 23A, although the conditions for the depositionand coating may vary depending on the material that is used to form thesecond HTL 23B-2.

A material for the second HTL 23B-2 may be a second compound representedby Formula 100 above. The above-detailed description of Formula 100above may be referred to here. In some embodiments, the second HTL 23B-2may include a second compound of Formula 100A-HLT or 100B-HLT. Theabove-detailed descriptions of Formulae 100A-HLT and 100B-HLT may bereferred to here. The second compound may be Compound 2-1 or 2-27, butis not limited thereto.

A sum (total) of thicknesses of the first HTL 23B-1 and the second HTL23B-2 may be from about 50 Å to about 2000 Å, and in some embodiments,from about 100 Å to about 1500 Å. In one embodiment, when the sum ofthicknesses of the first HTL 23B-1 and the second HTL 23B-2 is withinthese ranges, the first HTL 23B-1 and second HTL 23B-2 have satisfactoryhole transporting ability without a substantial increase in drivingvoltage.

A thickness ratio of the first HTL 23B-1 to the second HTL 23B-2 may befrom about 1:9 to about 9:1, and in some embodiments, from about 3:7 toabout 7:3, but is not limited thereto.

At least one of the HIL 23A, the first HTL 23B-1, and the second HTL23B-2 may further include a charge-generating material, in addition tothe above-described materials, to improve conductivity of the layers.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one of quinine derivatives, metal oxides, and compoundswith a cyano group, but are not limited thereto. Non-limiting examplesof the p-dopant are quinone derivatives such astetracyanoquinonedimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), orthe like; metal oxides such as tungsten oxide, molybdenum oxide, or thelike; and cyano-containing compounds such as Compound 200 below.

The charge-generating material may be homogeneously dispersed orinhomogeneously distributed in at least one of the HIL 23A, the firstHTL 23B-1 and the second HTL 23B-2. The charge-generating material maybe present in any form.

Then, the EML 25 may be formed on the second HTL 23B-2 by using vacuumdeposition, spin coating, casting, LB deposition, or the like. When theEML 25 is formed using vacuum deposition or spin coating, the depositionand coating conditions may be similar to those for the formation of theHIL 23A, though the conditions for deposition and coating may varydepending on the material that is used to form the EML 25.

The EML 25 may include a host and a dopant.

Non-limiting examples of the host are Alq₃,4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA,1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3, distyrylarylene(DSA), dmCBP (see a formula below), and Compounds 501 to 509 below.

In some embodiments, an anthracene-based compound represented by Formula400 below may be used as the host.

In Formula 400, Ar₁₁₁ and Ar₁₁₂ may be, each independently, asubstituted or unsubstituted C₆-C₆₀ arylene group; Ar₁₁₃ to Ar₁₁₆ maybe, each independently, a substituted or unsubstituted C₁-C₁₀ alkylgroup or a substituted or unsubstituted C₆-C₆₀ aryl group; and g, h, i,and j may be, each independently, an integer from 0 to 4.

In some embodiments, Ar₁₁₁ and Ar₁₁₂ in Formula 400 may be, eachindependently, selected from a phenylene group, a naphthylene group, aphenanthrenylene group, and a pyrenylene group; and a phenylene group, anaphthylene group, a phenanthrenylene group, a fluorenyl group, and apyrenylene group, substituted with at least one of a phenyl group, anaphthyl group, and an anthryl group.

In Formula 400 above, g, h, i, and j may be, each independently, 0, 1,or 2.

In some embodiments, Ar₁₁₃ to Ar₁₁₆ in Formula 400 may be, eachindependently, selected from

a C₁-C₁₀ alkyl group substituted with at least one of a phenyl group, anaphthyl group, and an anthryl group;

a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, aphenanthrenyl group and a fluorenyl group;

a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, aphenanthrenyl group, and a fluorenyl group, substituted with at leastone of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a phenyl group, a naphthyl group, an anthryl group, a pyrenylgroup, a phenanthrenyl group, and a fluorenyl group; and

but are not limited thereto.

For example, the anthracene-based compound of Formula 400 above may beone of the compounds represented by the following formulae, but is notlimited thereto:

In some embodiments, an anthracene-based compound represented by Formula401 below may be used as the host.

Ar₁₂₂ to Ar₁₂₅ in Formula 401 above may be defined as described above inconjunction with Ar₁₁₃ of Formula 400, and thus detailed descriptionsthereof will not be provided here.

Ar₁₂₆ and Ar₁₂₇ in Formula 401 above may be, each independently, aC₁-C₁₀ alkyl group, for example, a methyl group, an ethyl group, or apropyl group.

In Formula 401, k and l may be, each independently, an integer from 0 to4, for example, 0, 1, or 2.

For example, the anthracene compound of Formula 401 above may be one ofthe compounds represented by the following formulae, but is not limitedthereto:

The EML 25 may include the second compound represented by Formula 100above as a host. When the EML 25 includes the second compound of Formula100 as a host, the host in the EML 25 and the material of the second HTL23B-2 may be the same or differ from each other.

When the organic light-emitting diode is a full color organiclight-emitting diode, the second electrode may be patterned into a redsecond electrode, a green second electrode, and a blue second electrode.In some embodiments, the EML 23 may include a red second electrode, agreen second electrode, and/or a blue second electrode that are stackedupon one another to emit white light, but is not limited thereto.

The dopant in the EML 25 may be a suitable dopant.

Non-limiting examples of the blue dopant are compounds represented bythe following formulae.

Non-limiting examples of red dopant are compounds represented by thefollowing formulae. In some embodiments, the red dopant may be DCM orDCJTB, which will be described later.

Non-limiting examples of green dopant are compounds represented by thefollowing formulae. For example, the green dopant may be C545Trepresented below.

Non-limiting examples of the dopant that may be used in the EML arecomplexes represented by the following formulae:

Non-limiting examples of the dopant that may be used in the EML 25 areOs complexes represented by the following formulae:

When the EML 25 includes both a host and a dopant, the amount of thedopant may be, but is not limited to, from about 0.01 to about 15 partsby weight based on 100 parts by weight of the host.

A thickness of the EML 25 may be from about 100 Å to about 1000 Å, andin some embodiments, may be from about 200 Å to about 600 Å. In oneembodiment, when the thickness of the EML 25 is within these ranges, theEML 25 has improved light-emitting ability without a substantialincrease in driving voltage.

Then, an ETL 27A may be formed on the EML 25 using any of a variety ofmethods, such as vacuum deposition, spin coating, casting, or the like.When the ETL 27A is formed using vacuum deposition or spin coating, thedeposition and coating conditions may be similar to those for theformation of the HIL 23A, though the deposition and coating conditionsmay vary depending on the material that is used to form the ETL 23A. Amaterial for forming the ETL 27A may be any suitable material that canstably transport electrons injected from the second electrode 29.Non-limiting examples of materials for forming the ETL are a quinolinederivative, such as tris(8-quinolinorate)aluminum (Alq3), TAZ, BAIq,beryllium bis(benzoquinolin-10-olate (Bebq₂),9,10-di(naphthalene-2-yl)anthracene (ADN), Compound 201, and Compound202, but are not limited thereto.

The thickness of the ETL 27A may be from about 100 Å to about 1,000 Å,and in some embodiments, may be from about 150 Å to about 500 Å. In oneembodiment, when the thickness of the ETL 27A is within these ranges,the ETL 237A has satisfactory electron transporting ability without asubstantial increase in driving voltage.

The ETL 27A may further include a metal-containing material, in additionto such an electron transporting organic material as described above.

The metal-containing material may include a lithium (Li) complex.Non-limiting examples of the Li complex are lithium quinolate (LiQ) andCompound 203 below:

Then, an EIL 27B, which facilitates injection of electrons from theanode, may be formed on the ETL 27A. Any suitable electron-injectingmaterial may be used to form the EIL 27B.

Non-limiting examples of materials for forming the EIL 27B are LiF,NaCl, CsF, Li₂O, and BaO. The deposition and coating conditions forforming the EIL 27B may be similar to those for the formation of the HIL23A, though the deposition and coating conditions may vary according tothe material that is used to form the EIL 27B.

The thickness of the EIL 28B may be from about 1 Å to about 100 Å, andin some embodiments, may be from about 3 Å to about 90 Å. In oneembodiment, when the thickness of the EIL 27B is within these ranges,the EIL 27B has satisfactory electron injection ability without asubstantial increase in driving voltage.

The EML 25 may include the second compound of Formula 100 describedabove. For example, the EML 25 may include the second compound ofFormula 100A-H1 or 100B-H1.

FIG. 3 is a schematic view of a structure of an organic light-emittingdiode 30 according to another embodiment of the present invention.Referring to FIG. 3, the organic light emitting diode 30 has a structureincluding a substrate 31, a first electrode 32, a hole migration region33, an EML 35, an electron migration region 37, and a second electrode39 that are sequentially stacked on one another. The hole migrationregion 33 includes a HIL 33A and a HTL 33B that are sequentially stackedon the first electrode 32. The electron migration region 37 includes anETL 37A and an EIL 37B that are sequentially stacked on the EML 35.

The above-detailed descriptions of the substrate 21, the first electrode22, the HIL 23A, the ETL 27A, the EIL 27B, and the second electrode 29may be referred to as detailed descriptions of the substrate 31, thefirst electrode 32, the HIL 33A, the ETL 37A, the EIL 38B, and thesecond electrode 39 of FIG. 3.

A material for the HTL 33B may be a first compound represented byFormula 1 above. The above-detailed description of Formula 1 above maybe referred to here. For example, the HTL 33B may include a firstcompound of the Formula 1A, 1B, or 1C, wherein, in Formulae 1A, 1B and1C, Ar₁₀₁ and Ar₁₀₂ may be, each independently, a group represented byone of Formulae 4-1 to 4-7; xa and xb may be, each independently, 1 or2; R₁₀₁ may be a group represented by one of Formulae 6-1 to 6-8; R₁₀₉may be a group represented by one of Formulae 6-1 to 6-11; R₁₁₁ and R₁₁₂may be, each independently, one of a C₁-C₂₀ alkyl group; a C₁-C₂₀ alkylgroup substituted with at least one of a deuterium atom, a halogen atom,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof; a phenyl group, a naphthyl group, an anthrylgroup, a fluorenyl group, a carbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group,a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup, substituted with at least one of a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfuorenyl group, a diphenylfluorenyl group, a carbazolyl group, aphenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group; and R₁₀₂ to R₁₀₈ and R₁₁₃ to R₁₁₉ maybe hydrogen atoms.

In some embodiments, a material for the HTL 33B may be one of Compounds1-1 to 1-19 above.

The thickness of the HTL 33B may be from about 50 Å to about 2000 Å, andin some embodiments, may be from about 100 Å to about 1500 Å. In oneembodiment, when the thickness of the HTL 33B is within these ranges,the HTL 33B may have satisfactory hole transporting ability without asubstantial increase in driving voltage.

At least one of the HIL 33A and the HTL 33B may further include acharge-generating material as described above.

The EML 35 may include a host and a dopant, the host including a secondcompound represented by Formula 100 above. The above-detaileddescription of Formula 100 above may be referred to here. For example,the EML 35 may include the second compound of Formula 100A-H1 or 100B-H1as a host. The above-detailed descriptions of Formulae 100A-H1 and100B-H1 may be referred to here. For example, the EML 35 may includeCompound 2-5, 2-7, 2-23, or 2-30 as a host, but is not limited thereto.

The above-detailed descriptions on the dopant and thickness of the EML25 of FIG. 2 may be referred to here as descriptions of the dopant andthickness of the EML 35 of FIG. 3.

Although described with reference to the organic light-emitting diodes10, 20, and 30 of FIGS. 1, 2, and 3, the embodiments of the presentinvention are not limited thereto. Although not shown in FIGS. 2 and 3,a buffer layer may be further disposed between the second HTL 23B-2 andthe EML 25 of FIG. 2, or between the HTL 33B and the EML 35 of FIG. 3 inorder to compensate for an optical resonance distance according to thewavelength of light emitted from the EML 25 or 35 for higher efficiency.The buffer layer may include a suitable hole injection material, asuitable hole transporting material, the first compound of Formula 1above, or the second compound of Formula 100 above.

When the EML 25 or 35 includes a phosphorescent dopant, a hole blockinglayer (HBL) may be disposed between the EML 25 and the ETL 27A of FIG.2, or between the EML 35 and the ETL 37A of FIG. 3, in order to preventdiffusion of triplet exitons or holes into the ETL 27A or 37A. When theHBL is formed using vacuum deposition or spin coating, the conditionsfor deposition and coating may be similar to those for the formation ofthe HIL, although the conditions for deposition and coating may varyaccording to the material that is used to form the HBL. Any suitablehole-blocking material may be used. Non-limiting examples ofhole-blocking materials are oxadiazole derivatives, triazolederivatives, and phenanthroline derivatives. For example, bathocuproine(BCP) represented by the following formula may be used as a material forforming the HBL.

The thickness of the HBL may be from about 20 Å to about 1000 Å, and insome embodiments, may be from about 30 Å to about 300 Å. In oneembodiment, when the thickness of the HBL is within these ranges, theHBL has improved hole blocking ability without a substantial increase indriving voltage.

In some embodiments, the HIL 23A of FIG. 2 and/or the HIL 33A of FIG. 3may not be included. However, embodiments of the present invention arenot limited thereto, and may include any of a variety of structures.

As used herein, the unsubstituted C₁-C₆₀ alkyl group (or a C₁-C₆₀ alkylgroup) may be a linear or branched C1-C60 alkyl group, including amethyl group, an ethyl group, a propyl group, an isobutyl group, asec-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The substituted C₁-C₆₀ alkyl group may include at least one substituentselected from among a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, substituted with atleast one of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, and a phosphoric acid group or a salt thereof; a C₃-C₁₀cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀ heteroaryl group; aC₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, and a C₂-C₆₀heteroaryl group, substituted with at least one of a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfuorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; and —N(Q₁₁)(Q₁₂) and —Si(Q₁₁)(Q₁₂)(Q₁₃) (where Q₁₁ and Q₁₂ maybe, each independently, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroarylgroup, and Q₁₃ to Q₁₅ may be, each independently, a C₁-C₆₀ alkyl group,a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroarylgroup), but is not limited thereto.

As used herein, the unsubstituted C₁-C₆₀ alkoxy group (or a C₁-C₆₀alkoxy group) is represented by —OA (where A indicates a C₁-C₆₀ alkylgroup as described above), and may be, for example, a methoxy group, anethoxy group, or an isopropoxy group. At least one hydrogen atoms ofthese alkyl groups may be substituted with those substituents describedabove in conduction with the substituted C₁-C₆₀ alkyl group.

As used herein, the unsubstituted C₂-C₆₀ alkenyl group (or a C₂-C₆₀alkenyl group) refers to a C₂-C₆₀ alkyl group as described above with atleast one carbon double bond in the middle or terminal thereof. Examplesof the alkenyl group are an ethenyl group, a propenyl group, a butenylgroup, and the like. At least one hydrogen atom in the unsubstitutedC₂-C₆₀ alkenyl group may be substituted with those substituentsdescribed above in conjunction with the substituted C₁-C₆₀ alkyl group.

The unsubstituted C₂-C₆₀ alkynyl group is a C₂-C₆₀ alkyl group having atleast one carbon-carbon triple bond in the center or at a terminalthereof. Examples of the unsubstituted C₂-C₆₀ alkynyl group are anethenyl group, a propynyl group, and the like. At least one hydrogenatom in the alkynyl group may be substituted with those substituentsdescribed above in conjunction with the substituted C₁-C₆₀ alkyl group.

The unsubstituted C₆-C₆₀ aryl group is monovalent carbocyclic aromaticsystem having 6 to 60 carbon atoms including at least one aromatic ring.The unsubstituted C₆-C₆₀ arylene group is a divalent group having adivalent carbocyclic aromatic system having 6 to 60 carbon atomsincluding at least one aromatic ring. When the aryl group and thearylene group have at least two rings, they may be fused to each othervia a single bond. At least one hydrogen atom in the aryl group and thearylene group may be substituted with those substituents described abovein conjunction with the C₁-C₆₀ alkyl group.

Examples of the substituted or unsubstituted C₆-C₆₀ aryl group are aphenyl group, a C₁-C₁₀ alkylphenyl group (e.g., an ethylphenyl group), aC₁-C₁₀ alkylbiphenyl group (e.g., an ethylbiphenyl group), a halophenylgroup (e.g., an o-, m- or p-fluorophenyl group and a dichlorophenylgroup), a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, aphenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a(N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, apentalenyl group, an indenyl group, a naphthyl group, a halonaphthylgroup (e.g., a fluoronaphthyl group), a C₁-C₁₀ alkylnaphthyl group(e.g., a methylnaphthyl group), a C₁-C₁₀ alkoxynaphthyl group (e.g., amethoxynaphthyl group), an anthracenyl group, an azulenyl group, aheptalenyl group, an acenaphthylenyl group, a phenalenyl group, afluorenyl group, an anthraquinolinyl group, a methylanthryl group, aphenanthryl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, achloroperylenyl group, a pentaphenyl group, a pentacenyl group, atetraphenylenyl group, a hexaphenyl group, hexacenyl group, a rubicenylgroup, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group,a heptacenyl group, a pyranthrenyl group, and an ovalenyl group.Examples of the substituted C₆-C₆₀ aryl group may be inferred based onthose of the unsubstituted C₆-C₆₀ aryl group and the substituted C₁-C₃₀alkyl group described above. Examples of the substituted orunsubstituted C₆-C₆₀ arylene group may be inferred based on thoseexamples of the substituted or unsubstituted C₆-C₆₀ aryl group describedabove.

The unsubstituted C₂-C₆₀ heteroaryl group is a monovalent group havingat least one aromatic ring having at least one of the heteroatomsselected from the group consisting of N, O, P, and S. The unsubstitutedC₂-C₆₀ heteroarylene group is a divalent group having at least onearomatic ring having at least one of the heteroatoms selected from thegroup consisting of N, O, P, and S. In this regard, when the heteroarylgroup and the heteroarylene group have at least two rings, they may befused to each other via a single bond. At least one hydrogen atom in theheteroaryl group and the heteroarylene group may be substituted withthose substituents described with reference to the C₁-C₆₀ alkyl group.

Examples of the unsubstituted C₂-C₆₀ heteroaryl group are a pyrazolylgroup, an imidazolyl group, an oxazolyl group, a thiazolyl group, atriazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinylgroup, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, acarbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinylgroup, a benzoimidazolyl group, an imidazopyridinyl group and animidazopyrimidinyl group. Examples of the substituted or unsubstitutedC₂-C₅₀ heteroarylene group may be inferred based on those examples ofthe substituted or unsubstituted C₂-C₆₀ arylene group described above.

The substituted or unsubstituted C₆-C₆₀ aryloxy group indicates —OA₂(where A₂ is a substituted or unsubstituted C₆-C₆₀ aryl group describedabove). The substituted or unsubstituted C₆-C₆₀ arylthio group indicates—SA₃ (where A₃ is a substituted or unsubstituted C₆-C₆₀ aryl groupdescribed above).

Hereinafter, the present invention will be described in more detail withreference to the following synthesis examples and other examples.However, these examples are for illustrative purposes only and are notintended to limit the scope of the present invention.

EXAMPLES Synthesis Example 1 Synthesis of Compound 2-1

Compound 2-1 was synthesized according to the following reaction scheme:

Synthesis of Intermediate 2-1-a

13.6 g (1.2 eq) of Intermediate SM2-1(3-Iodo-9-phenyl-9H-carbazol-2-ol), 1.36 g (0.04 eq) of Pd(PPh₃)₄, 450mg (0.08 eq) of CuI were put into a flask, which was then supplied withN₂ gas in a vacuum, and 200 mL of THF was added thereto and stirred. 2.2mL (1.2 eq) of triethylamine and 1 eq of Intermediate L2-1 were slowlydropwise added thereinto, and then stirred in N₂ atmosphere at roomtemperature for about 2 hours. After removing the solvent using a rotaryevaporator, the reaction solution was added with 100 mL of water, andthen extracted three times with 100 mL of ethyl ether. An organic layerwas collected, and then dried using magnesium sulfate to evaporate thesolvent. The residue was separated and purified by silica gel columnchromatography to obtain Intermediate 2-1-a.

Synthesis of Intermediate 2-1-b

After dissolving 5 g of Intermediate 2-1-a in 100 mL of methylenechloride (MC), the temperature was cooled down to 0° C., followed byadding 7.84 g of Tf₂O and 2 mL of pyridine and stirring at about 0° C.for about 1 hour. After increasing the temperature of the reactionsolution to room temperature, the reaction solution was extracted threetimes with 100 mL of water and 100 mL of MC. An organic layer wascollected, and then dried using magnesium sulfate to evaporate thesolvent. The residue was separated and purified by silica gel columnchromatography to obtain Intermediate 2-1-b.

Synthesis of Intermediate 2-1-c

5 g of Intermediate 2-1-b, 1.5 g (1.2 eq) of Compound a, 590 mg (0.05eq) of Pd(PPh₃)₄, and 7.0 g (5 eq) of K₂CO₃ were dissolved in 100 mL ofTHF and 30 mL of distilled water, and then stirred under reflux forabout 24 hours after a temperature increase to about 120° C. Thereaction solution was cooled down to room temperature, and thenextracted three times with 200 mL of water and 200 mL of diethylether.An organic layer was collected, and then dried using magnesium sulfateto evaporate the solvent. The residue was separated and purified bysilica gel column chromatography to obtain Intermediate 2-1-c.

Synthesis of Compound 2-1

3 g of Intermediate 2-1-c was dissolved in 50 mL of MC, and 12.5 mL (20eq) of trifluoroacetic acid was slowly dropwise added thereinto andstirred at room temperature for about 1 hour. After completion of thereaction, the reaction solution was extracted three times each with 100mL of water and 100 mL of diethylether. An organic layer was collected,and then dried using magnesium sulfate to evaporate the solvent. Theresidue was separated and purified by silica gel column chromatographyto obtain Compound 2-1.

Synthesis Example 2 Synthesis of Compound 2-5

Compound 2-5 was synthesized according to the following reaction scheme:

Synthesis of Intermediate 2-5-a

Intermediate 2-5-a was obtained in the same manner as in the synthesisof Intermediate 2-1-a, except that Intermediates SM2-5 and L2-5 insteadof Intermediates

SM2-1 and L2-1, respectively, were used.

Synthesis of Intermediate 2-5-b

Intermediate 2-5-b was obtained in the same manner as in the synthesisof Intermediate 2-1-b, except that Intermediate 2-5-a instead ofIntermediate 2-1-a was used.

Synthesis of Intermediate 2-5-c

Intermediate 2-5-c was obtained in the same manner as in the synthesisof Intermediate 2-1-c, except that Intermediate 2-5-b and Compound binstead of Intermediate 2-1-b and Compound a, respectively, were used.

Synthesis of Compound 2-5

Intermediate 2-5 was obtained in the same manner as in the synthesis ofCompound 2-1, except that Intermediate 2-5-c instead of Intermediate2-1-c was used.

Synthesis Example 3 Synthesis of Compound 2-7

Compound 2-7 was synthesized according to the following reaction scheme:

Synthesis of Intermediate 2-7-a

Intermediate 2-7-a was obtained in the same manner as in the synthesisof Intermediate 2-1-a, except that Intermediates SM2-7 and L2-5 insteadof Intermediates SM2-1 and L2-1, respectively, were used.

Synthesis of Intermediate 2-7-b

Intermediate 2-7-b was obtained in the same manner as in the synthesisof Intermediate 2-1-b, except that Intermediate 2-7-a instead ofIntermediate 2-1-a was used.

Synthesis of Intermediate 2-7-c

Intermediate 2-7-c was obtained in the same manner as in the synthesisof Intermediate 2-1-c, except that Intermediate 2-7-b and Compound binstead of Intermediate 2-1-b and Compound a, respectively, were used.

Synthesis of Compound 2-7

Compound 2-7 was obtained in the same manner as in the synthesis ofCompound 2-1, except that Intermediate 2-7-c instead of Intermediate2-1-c was used.

Synthesis Example 4 Synthesis of Compound 2-23

Compound 2-23 was synthesized according to the following reactionscheme:

Synthesis of Intermediate 2-23-a

10 g of Intermediate SM2-23, 1.2 eq of Compound c, 1.5 mg (0.05 eq) ofPd(PPh₃)₄, and 18 g (5 eq) of K₂CO₃ were dissolved in 200 mL of THF and60 mL of distilled water, and then stirred under reflux for about 24hours after a temperature increase to about 120° C. The reactionsolution was cooled down to room temperature, and then extracted threetimes with 200 mL of water and 200 mL of diethylether. An organic layerwas collected, and then dried using magnesium sulfate to evaporate thesolvent. The residue was separated and purified by silica gel columnchromatography to obtain Intermediate 2-23-a.

Synthesis of Intermediate 2-23-b

5 g of Intermediate 2-23-a was dissolved in 100 mL of MC to obtain asolution, which was cooled down to about 0° C., followed by adding 8.4 gof Tf₂O and 2 mL of pyridine, and stirring at 0° C. for about 1 hour.After a temperature increase to room temperature, the reaction solutionwas extracted three times with 100 mL of water and 100 mL of MC. Anorganic layer was collected, and then dried using magnesium sulfate toevaporate the solvent. The residue was separated and purified by silicagel column chromatography to obtain Intermediate 2-23-b.

Synthesis of Intermediate 2-23-c

1.2 eq of Intermediate 2-23-b.470 g (0.04 eq) of Pd(PPh₃)₄, and 160 mg(0.08 eq) of CuI were put into a flask, which was then supplied with N₂gas in a vacuum, and 200 mL of THF was added thereto and stirred. 0.9 mL(1.2 eq) of triethylamine and 1 eq of Intermediate L2-5 were slowlydropwise added thereinto, and then stirred in N₂ atmosphere at roomtemperature for about 2 hours. After removing the solvent using a rotaryevaporator, 100 mL of water was added to the reaction solution, whichwas then extracted three times with 100 mL of ethylether. An organiclayer was collected, and then dried using magnesium sulfate to evaporatethe solvent. The residue was separated and purified by silica gel columnchromatography to obtain Intermediate 2-23-c.

Synthesis of Compound 2-23

3 g of Intermediate 2-23-c was dissolved in 50 mL of MC, and 7.4 mL (20eq) of trifluoroacetic acid was slowly dropwise added thereinto andstirred at room temperature for about 1 hour. After completion of thereaction, the reaction solution was extracted three times with 100 mL ofwater and 100 mL of diethylether. An organic layer was collected, andthen dried using magnesium sulfate to evaporate the solvent. The residuewas separated and purified by silica gel column chromatography to obtainCompound 2-23.

Synthesis Example 5 Synthesis of Compound 2-27

Compound 2-27 was synthesized according to the following reactionscheme:

Synthesis of Intermediate 2-27-a

Intermediate 2-27-a was obtained in the same manner as in the synthesisof Intermediate 2-23-a, except that Intermediate SM2-1 and Compound dinstead of Intermediate SM2-23 and Compound c, respectively, were used.

Synthesis of Intermediate 2-27-b

Intermediate 2-27-b was obtained in the same manner as in the synthesisof Intermediate 2-23-b, except that Intermediate 2-27-a instead ofIntermediate 2-23-a was used.

Synthesis of Intermediate 2-27-c

Intermediate 2-27-c was obtained in the same manner as in the synthesisof Intermediate 2-23-c, except that Intermediates 2-27-b and L2-27instead of Intermediates 2-23-b and L2-5, respectively, were used.

Synthesis of Compound 2-27

Compound 2-27 was obtained in the same manner as in the synthesis ofCompound 2-23, except that Intermediate 2-27-c instead of Intermediate2-23-c was used.

Synthesis Example 6 Synthesis of Compound 2-30

Compound 2-30 was synthesized according to the following reactionscheme:

Synthesis of Intermediate 2-30-a

Intermediate 2-30-a was obtained in the same manner as in the synthesisof Intermediate 2-23-a, except that Intermediate SM2-30 and Compound binstead of Intermediate SM2-23 and Compound c, respectively, were used.

Synthesis of Intermediate 2-30-b

Intermediate 2-30-b was obtained in the same manner as in the synthesisof Intermediate 2-23-b, except that Intermediate 2-30-a instead ofIntermediate 2-23-a was used.

Synthesis of Intermediate 2-30-c

Intermediate 2-30-c was obtained in the same manner as in the synthesisof Intermediate 2-23-c, except that Intermediates 2-30-b and L2-30instead of Intermediates 2-23-b and L2-5, respectively, were used.

Synthesis of Compound 2-30

Compound 2-30 was obtained in the same manner as in the synthesis ofCompound 2-23, except that Intermediate 2-30-c instead of Intermediate2-23-c was used.

Example 1

To manufacture an anode, a glass substrate with deposited ITO/Ag/ITOlayers (70/1000/70 Å) was cut to a size of 50 mm×50 mm×0.5 mm and thenultrasonicated in isopropyl alcohol for five minutes and in pure waterfor five minutes, and then cleaned by irradiation of ultraviolet raysfor 30 minutes and exposure to ozone. The resulting glass substrate wasloaded into a vacuum deposition device.

After 2-TNATA was vacuum-deposited on the anode to form an HIL having athickness of 600 Å, Compound 1-8 was deposited on the HIL to form afirst HTL having a thickness of about 600 Å, and then Compound 2-1 wasdeposited on the first HTL to form a second HTL having a thickness ofabout 750 Å.

CBP (host) and PtOEP (dopant) were co-deposited in a weight ratio ofabout 91:9 on the second HTL to form an EML having a thickness of about400 Å, followed by depositing BCP on the EML to form a HBL having athickness of about 50 Å. After depositing Alq₃ on the HBL to form an ETLhaving a thickness of about 350 Å, LiF was deposited on the ETL to forman EIL having a thickness of about 10 Å, followed by depositing Mg andAl in a weight ratio of about 90:10 on the EIL to form a cathode havinga thickness of about 120 Å, thereby manufacturing an organiclight-emitting device (emitting red light)

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 1-17 instead of Compound 1-8 was usedto form the first HTL.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 1-19 instead of Compound 1-8 was usedto form the first HTL, and Compound 2-27 instead of Compound 2-1 wasused to form the second HTL.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that, instead of forming the first and second HTLs,a HTL having a thickness of about 1350 Å was formed by depositingCompound 1-8 on the HIL, and Compound 2-7 instead of CBP was used as ahost in forming the EML on the HTL

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 4, except that Compound 1-17 instead of Compound 1-8 was usedto form the HTL.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 4, except that Compound 1-19 instead of Compound 1-8 was usedto form the HTL, and Compound 2-30 instead of Compound 2-7 was used as ahost in forming the EML.

Example 7

To manufacture an anode, a glass substrate with deposited ITO/Ag/ITOlayers (70 Å/1000 Å/70 Å) was cut to a size of 50 mm×50 mm×0.5 mm andthen ultrasonicated in isopropyl alcohol and pure water each for fiveminutes, and then cleaned by irradiation of ultraviolet rays for 30minutes and exposure to ozone. The resulting glass substrate was loadedinto a vacuum deposition device.

2-TNATA was vacuum-deposited on the anode to form an HIL having athickness of 600 Å, and then Compound 1-8 was deposited on the HIL toform a HTL having a thickness of 1000 Å.

Compound 2-5 (host) and Ir(ppy)₃ (dopant) were co-deposited in a weightratio of about 91:9 on the HTL to form an EML having a thickness ofabout 250 Å, followed by depositing BCP on the EML to form a HBL havinga thickness of about 50 Å. After depositing Alq₃ on the hole blockinglayer to form an ETL having a thickness of about 350 Å, LiF wasdeposited on the ETL to form an EIL having a thickness of about 10 Å,followed by depositing Mg and Al in a weight ratio of about 90:10 on theEIL to form a cathode having a thickness of about 120 Å, therebymanufacturing an organic light-emitting device (emitting green light).

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 1-17 instead of Compound 1-8 was usedto form the HTL, and Compound 2-23 instead of Compound 2-5 was used as ahost in forming the EML.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound 1-19 instead of Compound 1-8 was usedto form the HTL, and Compound 2-23 instead of Compound 2-5 was used as ahost in forming the EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 7, except that Compound A represented by Formula A below,instead of Compound 1-8, was used to form the HTL, and CBP instead ofCompound 2-5 was used as a host in forming the EML.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 4, except that Compound A instead of Compound 1-8 was used toform the HTL, and CBP instead of Compound 2-7 was used as a host informing the EML.

Evaluation Example 1

Driving voltages, current densities, luminances, emitting-light colors,efficiencies, and half-life spans (@10 mA/cm²) of the organiclight-emitting devices of Examples 1 to 8 and Comparative Examples 1 and2 were measured using a PR650 (Spectroscan) Source Measurement Unit(available from Photo Research, Inc.). The results are shown in Tables 1and 2 below. LT₉₇ was evaluated as the time taken until a measuredinitial luminance (assumed as 100%) was reduced to 97% during driving atabout 10 mA/cm².

TABLE 1 HTL First Second Driving voltage Current density Luminance HTLHTL Host Dopant (V) (mA/cm²) (cd/m²) Example Compound Compound CBP PtOEP6.1 10 3,021 1 1-8 2-1 Example Compound Compound CBP PtOEP 6.2 10 3,1092 1-17 2-1 Example Compound Compound CBP PtOEP 6.0 10 2,983 3 1-19 2-27Example Compound Compound PtOEP 6.3 10 3,240 4 1-8 2-7 Example CompoundCompound PtOEP 6.5 10 3,037 5 1-17 2-7 Example Compound Compound PtOEP6.0 10 3,172 6 1-19 2-30 Example Compound Compound Ir(ppy)₃ 5.8 10 6,2187 1-8 2-5 Example Compound Compound Ir(ppy)₃ 5.9 10 6,431 8 1-17 2-23Example Compound Compound Ir(ppy)₃ 5.7 10 6,270 9 1-19 2-23 ComparativeCompound CBP Ir(ppy)₃ 6.5 10 4,652 Example A 1 Comparative Compound CBPPtOEP 7.0 10 2,213 Example A 2

TABLE 2 HTL First Second Efficiency Emission LT₉₇ HTL HTL Host Dopant(cd/A) color (hr) Example Compound Compound CBP PtOEP 30.2 Red 134 1 1-82-1 Example Compound Compound CBP PtOEP 31.1 Red 130 2 1-17 2-1 ExampleCompound Compound CBP PtOEP 29.8 Red 138 3 1-19 2-27 Example Compound1-8 Compound PtOEP 32.4 Red 135 4 2-7 Example Compound 1-17 CompoundPtOEP 30.4 Red 127 5 2-7 Example Compound 1-19 Compound PtOEP 31.7 Red138 6 2-30 Example Compound 1-8 Compound Ir(ppy)₃ 62.2 Green 84 7 2-5Example Compound 1-17 Compound Ir(ppy)₃ 64.3 Green 83 8 2-23 ExampleCompound 1-19 Compound Ir(ppy)₃ 62.7 Green 86 9 2-23 Compara- Compound ACBP Ir(ppy)₃ 46.5 Green 63 tive Example 1 Compara- Compound A CBP PtOEP22.1 Red 112 tive Example 2

Referring to Tables 1 and 2, the organic light-emitting devices ofExamples 1 to 6 were found to have lower driving voltages, higherluminances, higher efficiencies, higher color purities, and longerlifetimes than those of the organic light-emitting device of ComparativeExample 2. The organic light-emitting devices of Examples 6 to 9 werefound to have lower driving voltages, higher luminances, higherefficiencies, higher color purities, and longer lifetimes than those ofthe organic light-emitting device of Comparative Example 1.

As described above, according to the one or more of the aboveembodiments of the present invention, an organic light-emitting device(including a first compound of Formula 1 and a second compound ofFormula 100) has a low driving voltage, high luminance, high efficiency,and long lifetime.

It should be understood that the example embodiments described hereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments. It will be understood by those ofordinary skill in the art that various changes in form and details maybe made therein without departing from the spirit and scope of thepresent disclosure as defined by the following claims and equivalentsthereof.

What is claimed is:
 1. An organic light-emitting device comprising: asubstrate; a first electrode on the substrate; a second electrode facingthe first electrode; an emission layer between the first electrode andthe second electrode; a hole migration transfer region between the firstelectrode and the emission layer; and an electron migration regionbetween the emission layer and the second electrode, wherein the holemigration region comprises a first compound represented by Formula 1,and at least one of the hole migration region and the emission layercomprises a second compound represented by Formula 100 below:

wherein, in Formula 1, Ar₁₀₁ and Ar₁₀₂ are, each independently, asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₂-C₁₀ heterocyclooalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₂-C₁₀ heterocyclooalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, or a substituted or unsubstitutedC₂-C₆₀ heteroarylene group; xa and xb are, each independently, aninteger from 0 to 5; R₁₀₁ and R₁₀₉ are, each independently, asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, or a substituted or unsubstituted C₂-C₆₀ heteroaryl group;and R₁₀₂ to R₁₀₈, and R₁₁₁ to R₁₁₉ are, each independently, a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —N(Q₁)(Q₂), or —Si(Q₃)(Q₄)(Q₅)(where Q₁ to Q₅ are, each independently, a C₁-C₆₀ alkyl group, a C₁-C₆₀alkoxy group, a C₆-C₆₀ aryl group, or a C₂-C₆₀ heteroaryl group), and inFormula 100, i) R₅₆ and R₅₇ are linked to each other to form asubstituted or unsubstituted C₃-C₆₀ cyclic moiety, or a substituted orunsubstituted C₂-C₆₀ heterocyclic moiety, and R₅₁ to R₅₅ and R₅₈ to R₆₀are, each independently, a substituent represented by—(Ar₅₁)_(q)-(Ar₆₁); or ii) R₅₈ and R₅₉ are linked to each other to forma substituted or unsubstituted C₃-C₆₀ cyclic moiety, or a substituted orunsubstituted C₂-C₆₀ heterocyclic moiety, and R₅₁ to R₅₇ and R₆₀ are,each independently, a substituent represented by —(Ar₅₁)_(q)—(Ar₆₁);Ar₅₀ and Ar₅₁ are, each independently, a substituted or unsubstitutedC₃-C₁₀ cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocyclooalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a C₂-C₁₀ heterocyclooalkenylene group, asubstituted or unsubstituted C₆-C₆₀ arylene group, or a substituted orunsubstituted C₂-C₆₀ heteroarylene group; Ar₆₀ and Ar₆₁ are, eachindependently, selected from among a hydrogen atom, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₂-C₆₀ heteroaryl group,—N(Q₂₁)(Q₂₂), and —Si(Q₂₃)(Q₂₄)(Q₂₅) (where Q₂₁ and Q₂₂ are, eachindependently, selected from among a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, and a substituted or unsubstituted C₂-C₆₀ heteroaryl group;and Q₂₃ to Q₂₅ are, each independently, selected from among a hydrogenatom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, and a substituted or unsubstituted C₂-C₆₀ heteroaryl group); andp and q are, each independently, an integer from 0 to
 5. 2. The organiclight-emitting device of claim 1, wherein Ar₁₀₁ and Ar₁₀₂ in Formula 1are, each independently, represented by one of Formulae 3-1 to 3-24:

wherein, in Formulae 3-1 to 3-24, Y₁ is O, S, C(R₂₁)(R₂₂), or N(R₂₃);Z₁, Z₂, and R₂₁ to R₂₃ are, each independently, selected from among ahydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl groupand a C₁-C₂₀ alkoxy group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a C₆-C₂₀ aryl group and aC₂-C₂₀ heteroaryl group; a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroarylgroup, substituted with at least one of a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; and —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁ to Q₁₅ are,each independently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aC₆-C₂₀ aryl group, or a C₂-C₂₀ heteroaryl group); d1 is an integer from1 to 4; d2 is an integer from 1 to 3; d3 is an integer from 1 to 6; d4is an integer from 1 to 8; and d5 is 1 or
 2. 3. The organiclight-emitting device of claim 1, wherein Ar₁₀₁ and Ar₁₀₂ in Formula 1are, each independently, represented by one of Formulae 4-1 to 4-7:


4. The organic light-emitting device of claim 1, wherein, in Formula 1,i) xa=0 and xb=0; ii) xa=1 and xb=0; iii) xa=2 and xb=0; iv) xa=0 andxb=1; v) xa=0 and xb=2; or vi) xa=1 and xb=1.
 5. The organiclight-emitting device of claim 1, wherein, Formula 1, R₁₀₁ and R₁₀₉ are,each independently, represented by one of Formulae 5-1 to 5-22:

wherein, in Formulae 5-1 to 5-22, Y₂ is O, S, C(R₂₅)(R₂₆), or N(R₂₇);Z₁₁ to Z₁₄, and R₂₅ to R₂₇ are, each independently, selected from amonga hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl groupand a C₁-C₂₀ alkoxy group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a C₆-C₂₀ aryl group and aC₂-C₂₀ heteroaryl group; a C₆-C₂₀ aryl group and a C₂-C₂₀ heteroarylgroup, substituted with at least one of a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ an alkoxy group, a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenylgroup, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group; and —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁to Q₁₅ are, each independently, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a C₆-C₂₀ aryl group, or a C₂-C₂₀ heteroaryl group; e1 is aninteger from 1 to 5; e2 is an integer from 1 to 7; e3 is an integer from1 to 3; e4 is an integer from 1 to 4; and e5 is 1 or
 2. 6. The organiclight-emitting device of claim 1, wherein R₁₀₁ in Formula 1 isrepresented by one of Formulae 6-1 to 6-8, and R₁₀₉ in Formula 1 isrepresented by one of Formulae 6-1 to 6-11:

wherein, in Formulae 6-1 to 6-11, Z_(11a), to Z_(11c), and R₂₅ and R₂₆are, each independently, selected from among a deuterium atom, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine, a hydrazone, a carboxyl group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof; a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group; and a phenyl group, a naphthyl group,an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group,substituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenylgroup, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group; and Q₁₁ and Q₁₂ are, each independently, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, or an isoquinolinyl group.7. The organic light-emitting device of claim 1, wherein R₁₁₁ and R₁₁₂in Formula 1 are, each independently, selected from among a C₁-C₂₀ alkylgroup; a C₁-C₂₀ alkyl group substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylgroup or a salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a carbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; and a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, aquinolinyl group, and an isoquinolinyl group, substituted with at leastone of a deuterium atom, a halogen atom, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazine, ahydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup.
 8. The organic light-emitting device of claim 1, wherein thesecond compound is a compound represented by Formula 100A or 100B below:

wherein, in Formulae 100A and 100B, P ring and Q ring are, eachindependently, selected from among i) benzene, naphthalene, fluorene,carbazole, dibenzofuran, and dibenzothiophene; and ii) benzene,naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene,substituted with at least one selected from among a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, and a C₁-C₆₀ alkoxy group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof, a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup, and —N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ are, each independently, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group).
 9. The organic light-emitting deviceof claim 1, wherein the second compound is a compound represented by oneof Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9:

wherein, in Formulae 100A-1 to 100A-8 and 100B-1 to 100B-9, X₁₂ is O, S,C(R₇₁)(R₇₂), or N(R₇₃); R₆₁, R₆₂, and R₇₁ to R₇₃ are, eachindependently, selected from among a hydrogen atom, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,substituted with at least one of a deuterium atom, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof; a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, anda C₂-C₆₀ heteroaryl group; a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, and a C₂-C₆₀ heteroaryl group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group,a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group,a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; and —N(Q₁₁)(Q₁₂),and —Si(Q₁₁)(Q₁₂)(Q₁₃) (where Q₁₁ and Q₁₂ are, each independently, aC₆-C₆₀ aryl group or a C₂-C₆₀ heteroaryl group, and Q₁₃ to Q₁₅ are, eachindependently, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀aryl group, or a C₂-C₆₀ heteroaryl group); r1 is an integer from 1 to 4;r2 is 1 or 2; and r3 is an integer from 1 to
 6. 10. The organiclight-emitting device of claim 1, wherein Ar₅₀ and Ar₅₁ in Formula 100are, each independently, selected from among, i) a phenylene group, anaphthylene group, a fluorenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, a carbazolylene group, a triazinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, and ii) aphenylene group, a naphthylene group, a fluorenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a quinolinylene group, a carbazolylene group, atriazinylene group, a dibenzofuranylene group, and adibenzothiophenylene group, substituted with at least one of a deuteriumatom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine, a hydrazone, a carboxylicgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthryl group, afluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group.
 11. The organiclight-emitting device of claim 1, wherein Ar₆₀ and Ar₆₁ in Formula 100are, each independently, selected from among groups represented byFormulae 103-1 to 103-16 below:

wherein, in Formulae 103-1 to 103-16, Y₂₁ is O, S, C(Z₄₁)(Z₄₂), orN(Z₄₃); Z₃₁, Z₃₂, and Z₄₁ to Z₄₃ are, each independently, selected fromamong a hydrogen atom, a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; Q₂₁ and Q₂₂ are, each independently, selected from among a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group; g1 is an integer from 1 to 5; g2 isan integer from 1 to 7; g3 is an integer from 1 to 3; g4 is an integerfrom 1 to 4; and g5 is 1 or
 2. 12. The organic light-emitting device ofclaim 1, wherein the first compound is one of Compounds 1-1 to 1-19below:


13. The organic light-emitting device of claim 1, wherein the secondcompound is one of Compounds 2-1 to 2-30:


14. The organic light-emitting device of claim 1, wherein the holemigration region comprises i) a first hole transport layer, and ii) asecond hole transport layer between the first hole transport layer andthe emission layer, the first compound is in the first hole transportlayer, and the second compound is in the second hole transport layer.15. The organic light-emitting device of claim 14, wherein the secondcompound is in the emission layer.
 16. The organic light-emitting deviceof claim 14, wherein the second compound is a compound represented byFormula 100A-HLT or 100B-HLT below:

wherein, in Formulae 100A-HLT and 100B-HLT, P ring and Q ring are, eachindependently, selected from among i) benzene, naphthalene, fluorene,carbazole, dibenzofuran, and dibenzothiophene; and ii) benzene,naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene,substituted with at least one selected from among, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, and a C₁-C₆₀ alkoxy group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof, a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup, and —N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ are, each independently, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group), Ar₅₀ and Ar₅₁ are, eachindependently, selected from among i) a phenylene group, a naphthylenegroup, a fluorenylene group, a pyridinylene group, a pyrazinylene group,a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, acarbazolylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group, and ii) a phenylene group, anaphthylene group, a fluorenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, a carbazolylene group, a triazinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, substitutedwith at least one of a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxylic group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; p and q are, each independently, 0, 1, or 2; and Ar₆₁, Q₂₁, andQ₂₂ are, each independently, selected from among a phenyl group, anaphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenylgroup, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group.
 17. The organic light-emitting device of claim 14,wherein at least one of the first hole transport layer and the secondtransport layer further comprises a charge-generating material.
 18. Theorganic light-emitting device of claim 1, wherein the hole migrationregion comprises a hole transport layer, the first compound is in thehole transport layer, and the second compound is in the emission layer.19. The organic light-emitting device of claim 18, wherein the secondcompound is a compound represented by Formula 100A-H1 or 100B-H1 below:

wherein, in Formulae 100A-H1 and 100B-H1, P ring and Q ring are, eachindependently, selected from among, i) benzene, naphthalene, fluorene,carbazole, dibenzofuran, and dibenzothiophene; and ii) benzene,naphthalene, fluorene, carbazole, dibenzofuran, and dibenzothiophene,substituted with at least one selected from among a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, and a C₁-C₆₀ alkoxy group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof, a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group, a phenyl group, a naphthyl group, ananthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group,a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group, substituted withat least one of a deuterium atom, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinoinlylgroup, and —N(Q₁₁)(Q₁₂) (where Q₁₁ and Q₁₂ are, each independently, aphenyl group, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, or an isoquinolinyl group), Ar₅₀ and Ar₅₁ are, eachindependently, selected from among, i) a phenylene group, a naphthylenegroup, a fluorenylene group, a pyridinylene group, a pyrazinylene group,a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, acarbazolylene group, a triazinylene group, a dibenzofuranylene group,and a dibenzothiophenylene group, and ii) a phenylene group, anaphthylene group, a fluorenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, a carbazolylene group, a triazinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, substitutedwith at least one of a deuterium atom, a halogen atom, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxylic group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; p and q are, each independently, 0, 1, or 2; Z₂₁ to Z₂₂ are, eachindependently, selected from among a hydrogen atom, a deuterium atom, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine, a hydrazone, a carboxylic group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, an anthryl group, a fluorenylgroup, a dimethylfluorenyl group, a diphenylfluorenyl group, acarbazolyl group, a phenylcarbazolyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group; f1 and f2 are,each independently, 0, 1, or 2; and Ar₆₀ and Ar₆₁ are, eachindependently, selected from among groups represented by Formulae 103-1to 103-16 below:

wherein, in Formulae 103-1 to 103-16, Y₂₁ is O, S, C(Z₄₁)(Z₄₂), orN(Z₄₃); Z₃₁, Z₃₂, and Z₄₁ to Z₄₃ are, each independently, selected fromamong a hydrogen atom, a deuterium atom, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine, a hydrazone, a carboxylic group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, adiphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup; Q₂₁ and Q₂₂ are, each independently, selected from among a phenylgroup, a naphthyl group, an anthryl group, a fluorenyl group, adimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group,a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group; g1 is an integer from 1 to 5; g2 isan integer from 1 to 7; g3 is an integer from 1 to 3; g4 is an integerfrom 1 to 4; and g5 is 1 or
 2. 20. The organic light-emitting device ofclaim 18, wherein the hole transport layer further comprises acharge-generating material.